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Tell Us About Your Child's School

OCPS families—help shape the future of our schools by participating in the Fall 2025 Family Survey. Your feedback helps us improve learning experiences, strengthen communication, and better support every student. It only takes a few minutes, but your input makes a lasting impact.

Click here to share your feedback!
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What is ParentSquare?

ParentSquare is a unified communication platform that offers a variety of tools that allow the district, school administrators and teachers to more effectively communicate and engage with families and students.

Click here to learn more!
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School Spirit Run

The 5th Annual School Spirit Run is officially set for Saturday, February 7, 2026. We can’t wait to see our community come together in full stride!

Register Today!
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Parents, now is the time!

At OCPS, we believe that every student deserves a thriving future, and it all starts with the right educational foundation. Click below to enroll your child and become part of a community that’s united in purpose and passionate about student success.

Enroll Now!
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Need to Locate Resources? You can search for free or reduced cost programs such as food, housing, mental health, education programs, and other social services provided directly by Community Based Organizations.

Click here to learn more!
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Hurricane Season: June 1 - November 30

Hurricanes are dangerous and can cause major damage from storm surge, wind damage, rip currents and flooding.

Click here for helpful resources!
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OCPS Parent Portal Concerns?

If you are experiencing issues with an OCPS Parent Portal Application (i.e. Skyward Family Access, Canvas Parent) please click below for support.

Parent Portal Concerns Form

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Latest News

Stay up to date on the latest news, events and more with the ParentSquare app!

Upcoming Events

View the full calendar to see all events happening in the next few weeks and months!

School Profile

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Vision: Every student graduates prepared and inspired for a thriving future.

Mission: Together with our families and the community, we empower students with a superior academic experience, essential life skills, and boundless opportunities.

Address: 5240 Keenes Pheasant Drive Windermere, FL 34786

Phone: 407-654-1351

Principal:Dr. Tracy Webley

Mascot: Cougar

Colors: Blue and Silver

School Hours:  8:45-3:00 (MTRF) and 8:45-2:00 (W)

Grades: Kindergarten – 5th 

Principal’s Message
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Dear Parents and Families,

Welcome to Keenes Crossing Elementary School.  Whether you are returning or joining us for the first time, we are thrilled to have you as part of our school community. At Keenes Crossing, we believe that strong partnerships between home and school are the foundation of student success, and we are committed to working together to ensure every child has an enriching, joyful, and safe educational experience.

Our dedicated teachers and staff work hard on engaging lessons, organizing classrooms, and planning exciting events that foster curiosity, creativity, and a love of learning. Each year, we are especially focused on developing strong literacy and math foundations, building character, and encouraging active participation in our school community.

To help your child have a successful school year, we encourage the following:

  • Stay Connected:  Regularly check our school website, read the weekly grade level newsletters, and sign up Parent Square for updates, important dates, and classroom news.
  • Read Together:  Even just 15 or 20 minutes of reading at home each day can make a big difference in your child’s reading development.
  • Get Involved: Join the PTO, volunteer in the classroom, or attend school events. Your involvement shows your child that education matters.
  • Maintain Healthy Routines: A consistent bedtime, a nutritious breakfast, and daily attendance all support your child’s focus and well-being.
  • Attendance Matters:  Make sure your schloar is attending school and is on time!

Please never hesitate to reach out to your child’s teacher or to me if you have questions, ideas, or concerns. Our doors are always open, and we value your voice.

Thank you for trusting us with your child’s education. Let’s make each school year one of growth, discovery, and joy!

Warmly,

Dr. Webley